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Volumn 44, Issue 28, 2003, Pages 5235-5238

The first synthesis of (±)-brevione B, an allelopathic agent isolated from Penicillium sp.

Author keywords

Allelopathic agents; Diterpenoids; Tandem reaction; pyrone

Indexed keywords

DITERPENOID; HERBICIDE;

EID: 0038684510     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01275-9     Document Type: Article
Times cited : (33)

References (17)
  • 2
    • 0037169964 scopus 로고    scopus 로고
    • and references cited therein
    • Vyvyan J.R. Tetrahedron. 58:2002;1631. and references cited therein.
    • (2002) Tetrahedron , vol.58 , pp. 1631
    • Vyvyan, J.R.1
  • 6
    • 85031171922 scopus 로고    scopus 로고
    • For the palladium-mediated reactions: (a) Tsuji, J. Palladium Reagents and Catalyst, Innovations in Organic Synthesis; John Wiley & Sons: Chichester, 1995: pp. 250-422; (b) Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp. 799-853; (c) Tsuji, J.; Kataoka, H.; Kobayashi, Y. Tetrahedron Lett. 1981, 22, 2575; (d) Trost, B. M.; Molander, G. A. J. Am. Chem. Soc. 1981, 103, 5969; (e) Mereno-Mañas, M.; Prat, M.; Ribas, J.; Virgili, A. Tetrahedron Lett. 1988, 29, 581
    • For the palladium-mediated reactions: (a) Tsuji, J. Palladium Reagents and Catalyst, Innovations in Organic Synthesis; John Wiley & Sons: Chichester, 1995: pp. 250-422; (b) Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp. 799-853; (c) Tsuji, J.; Kataoka, H.; Kobayashi, Y. Tetrahedron Lett. 1981, 22, 2575; (d) Trost, B. M.; Molander, G. A. J. Am. Chem. Soc. 1981, 103, 5969; (e) Mereno-Mañas, M.; Prat, M.; Ribas, J.; Virgili, A. Tetrahedron Lett. 1988, 29, 581.
  • 12
    • 85031171009 scopus 로고    scopus 로고
    • 16 was not successful by usual procedures such as the Wittig reaction, Peterson reaction and Tebbe reagent
    • The direct methylenation of 12 to 16 was not successful by usual procedures such as the Wittig reaction, Peterson reaction and Tebbe reagent.
  • 14
    • 85031164134 scopus 로고    scopus 로고
    • 14, while they should be 90° and 30° in its β-isomer. The numbering in this paper corresponds to that of breviones reported in Ref. 2
    • 2 and12-H are both ca. 60° in 14, while they should be 90° and 30° in its β-isomer. The numbering in this paper corresponds to that of breviones reported in Ref. 2.
  • 15
    • 85031167519 scopus 로고    scopus 로고
    • It was noted that conventional epoxidation with m-CPBA, dimethyldioxirane, etc., did not work.
    • It was noted that conventional epoxidation with m-CPBA, dimethyldioxirane, etc., did not work.
  • 16
    • 85031174511 scopus 로고    scopus 로고
    • 14. The reason for the selectivity might be steric hindrance due to the angular methyl group
    • The α-orientation of the oxirane-ring was not certain at this stage, but it was confirmed by its conversion into 14. The reason for the selectivity might be steric hindrance due to the angular methyl group.
  • 17
    • 85031168805 scopus 로고    scopus 로고
    • 3) δ=9.7, 15.5, 16.0, 17.2, 18.4, 19.0, 21.5, 23.2, 26.4, 28.7, 31.8, 34.0, 36.5, 38.9, 40.9, 47.0, 47.4, 55.1, 99.5, 99.6, 102.8, 127.8, 131.8, 160.4, 162.0, 171.1, 217.2
    • 3) δ=9.7, 15.5, 16.0, 17.2, 18.4, 19.0, 21.5, 23.2, 26.4, 28.7, 31.8, 34.0, 36.5, 38.9, 40.9, 47.0, 47.4, 55.1, 99.5, 99.6, 102.8, 127.8, 131.8, 160.4, 162.0, 171.1, 217.2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.